


close enough

by SebGray



Category: Critical Role (Web Series)
Genre: Alternate Universe - Modern with Magic, Anal Fingering, Anal Play, Anal Sex, Bondage, Dom/sub, Established Relationship, F/M, Masturbation, Pegging, Plot What Plot/Porn Without Plot, Safewords, Strap-Ons
Language: English
Status: Completed
Published: 2019-10-29
Updated: 2019-10-29
Packaged: 2021-01-06 08:11:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,047
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21223385
Author URL: https://archiveofourown.org/users/SebGray/pseuds/SebGray
Summary: Caleb had never felt this vulnerable before, but his fiancee Jester knows exactly how to make him feel safe.





	close enough

**Author's Note:**

> Someone said write smut, so I wrote it. 3k words of smut in one night. You're welcome.

Jester ran two fingers underneath the rope that held Caleb in place, criss-crossing all over his body to make sure that nothing was ever too tight, too restrictive. “Color, my dear?” The nickname was spoken in Infernal, as she was now wont to do ever since they started dating.

“Green,” he said, breathing deep in part to test how restrictive the ropes were. Another part of it was...he hadn’t done anything involved bondage since Astrid. Since all that time ago, when neither of them were this safe. Being vulnerable with Jester wasn’t new -- gods only knew they wouldn’t have gotten engaged without doing that -- but being helpless was. He went through the reminders she had taught him when he had his first breakdown since they started dating.

You are safe.

You are loved.

You are protected.

You will not be judged.

“Yellow, actually,” he mumbled. “I need some reassurance, please.”

“Okay,” Jester said, shifting to sit down next to him. She took a lock of his hair and started braiding it, like she did every time he was panicking. The gesture was no longer weird but nice, but soothing now. “I love you, Caleb. You’re doing so well! You sat through that whole thing without squirming! And you even helped me out with not skipping steps. You’re a very good boy.”

In between the braiding and the praise, the panic subsided, and he relaxed, once again feeling that soft, pliant feeling he always got when he dommed her.

“Color?” she repeated.

He smiled. “Green as an emerald, my love.”

“Good boy,” she said, kissing his forehead, mumbling an “I love you” in Infernal before moving to the chair they had brought in from the living room. It was his reading chair, big and ridiculously comfy, with leather that was worn enough to not stick to your skin but new enough that you could clean up any messes without breaking out the stain remover. Ever since he’d first eaten her out on it, it’d been their go-to fucking location aside from their bed and the one section of kitchen counter that wasn’t cluttered with baking supplies. The only downside Caleb had come across since the chair became a part-time sex spot was that sometimes he’d accidentally remember one of their trysts while reading and would have to pause just to jerk off.

Aside from that, he had no complaints about the sight of Jester settling into in like it was her throne.

She had a toy out, her favorite dildo that he got her when they were briefly long distance. It looked pretty damn close to his cock, especially with it was slick with pre-cum or her spit. Jester put it on the arm of the chair as she turned around and pulled down the pink panties she’d been teasing him with the whole damn night. The sight of his cock visibly perking up made her giggle. “Wow, Caleb, just the sight of my cunt has you getting hard. I got you trained good.”

Caleb laughed. He had never laughed during sex before her. Gods, what a difference she’d made.

Now she was working on her bra. She cursed a little in Infernal, mumbling, “If this damn thing gets stuck to the fabric one more time, I’m gonna--” before getting it off with a victorious, “Aha!” He laughed again, but when she glared at him he stopped, having to press his lips together to conceal his grin. She tossed the bra aside and leaned back, legs spread, tits out. The sight sent a flush from forehead to clavicle and now he was suddenly aware that he was both very hard and completely unable to do a damn thing about it. She smiled, satisfied. “Good boy. Don’t worry, you’ll get your reward.”

He knew he would. The strap-on with the dildo that could make him cum six ways to Sunday was tantalizingly within his line of sight.

Jester started by playing with her clit, soft and slow as she made the tiniest little sounds. Normally, she’d relax and let her head fall back, let her eyes flutter shut, but she was too busy watching him, gauging his face for reactions, watching where his gaze shifted. “You look so pretty when you’re horny, Caleb,” she teased.

“I look even prettier with a dick in my ass,” he jokingly replied.

“You do. But I also love the way you look when you’re desperate. I just can’t resist it.” She moaned a little more as she picked up the pace, biting her lip as her trained fingers did their thing. He remembered all the videos she sent, all those years ago, when she would beg for his cock as she rubbed her clit, fingers clumsy at the time. 

In his author’s mind, Caleb would definitely call that character growth.

Caleb found himself moaning ever so slightly just at the sight of her. She noticed it -- of course she noticed it, she could read him like a damn book at this point -- and commented, “Am I gonna make you so horny you cum untouched again?”

Once more, Caleb laughed. The last time she did that, she bragged about it to damn near everyone. Didn’t help that he somehow managed to cum so hard he got ejaculate on the ceiling. That was an embarrassing thing to google.

Jester laughed as well. “Now you’re turning it into a challenge, Caleb. How do you feel about cumming untouched?” Before she could let him answer, she added, eyes lit up with an idea, “How do you feel about cumming untouched twice?”

After taking a moment to figure out if he could even do that, Caleb nodded and said, “Sure, if you think I can do it. I trust you.”

“I hope you do,” she said, snorting softly. “You’re completely tied up. If you didn’t trust me, I’d be really concerned.”

“Ja, true,” he replied. “We should probably get back into the mood,” he said after a brief pause, becoming all too aware of the mild ridiculousness of them being in this situation, him all but gift-wrapped for her, her completely naked on a chair, rubbing one out.

“True, true. Color, before I move on?”

“Green. I’m okay.” Caleb smiled at her reassuringly.

“Okay, okay.” She took a deep breath and put her domme face on as she grabbed her trusty dildo and a bottle of lube from the floor. She set the cock on her lap as she poured a good amount of lube into the other hand, slathering it onto the cock. As she rubbed the silicone, she looked at him with a wry smile. “I know you want my hand on your cock right now, my love,” she said, tacking on another Infernal pet name. “You want me to rub your cock until you cum, don’t you, Caleb?”

“Ja, Jester, I do,” he muttered.

“Louder, Caleb?” she said gently. One of the many things she had been training him to do was being louder in bed. Her soft reminders was one of her many tactics.

“I do, Jester.” He took in a deep breath as her voice returned to his head. We’re in a nice, quiet house in the middle of nowhere, Caleb. No one will hurt you. No one will judge you. “I want you to rub my cock until I cum.”

“Good boy!” she said, smiling. “As soon as I cum, it’ll be your turn, Caleb.” Jester moved the dildo to her cunt, rubbing it over her vulva but not fucking herself, not yet. “Caleb, I’m gonna flip you over and fuck your ass until you cum. You want that?”

He nodded eagerly. “Please, Jester. I want you to fuck me.”

“Oh, look at you, so desperate for my cock already. I’ve barely gotten started.” She smiled as she pressed the cock inside of her, easily taking it nearly up to the hilt.

Did she need to do that to turn him on more? Not at all.

Did it still work? Most definitely.

“Fuck, Jester,” he moaned, fists clenching as his back arched. He was leaking pre-cum like crazy. 

“You look so needy, Caleb,” Jester said. “I bet you want to fuck me, don’t you?” She moved the dick in and out, the movement fluid and practiced. One perfect graze made her moan loudly. “Oh, Caleb, you want your cock in my cunt, don’t you? You want me to ride you until you cum, don’t you, Caleb?”

Caleb nodded. “Ja, Jester. I just need something, anything--”

“Give me a moment to cum, Caleb,” she said, voice stern but not sharp, “and then I’ll start working on your ass.”

“Alright, Jester.” He tried to settle, tried to relax, but she was moaning more now, using her free hand to rub her clit as her pace increased. Caleb’s hips shifted slightly, as though he could possibly get off by thrusting into the air. Soon, waiting was impossible, and he just had to beg some more. “Please, Jester, I’ve been so good.”

“You just need to be good a little longer, Caleb. Or are you really that needy for a cock up your ass?”

“Jester, I need anything, please.” It wasn’t a lie. Just a gust of wind could probably make him cum at this point. His cock was aching and needy and so damn hard, he could barely stand it. All he could do was squirm.

“Oh, Caleb,” she said, panting softly. He knew she was getting close, and he halfway dared her to draw it out, keep him desperate and whining on the bed. “Caleb, my love, I’m gonna cum. Beg for me a little more, Caleb. Make me cum with how needy you are.”

Caleb whined, but managed to scrape some words into a sentence. “Jester, please, I need you. I need you to touch me, fuck me, please, Jester, I want to cum, I need your cock, please--”

With a loud cry, her body contracted, cunt squirting as she hit her climax. If Caleb’s dick weren’t devoid of contact, he probably would’ve came too.

“Caleb,” she muttered, as she wound down, pulling the cock out and plopping it to the side unceremoniously. She stayed there, sprawled on the chair, panting, cunt slick and shining.

Add that to the mental images he was absolutely going to masturbate to.

After regaining some of her composure, she got up, stretched, then slowly began to strut over to the bed. “You look beautiful like that, Caleb,” she said, once she came close enough to reach over to graze his skin with her forefinger, still wet with lube and her cum. “I almost wish I was the one getting dick, tonight. I’m sure you’d give me quite the load, wouldn’t you, Caleb?”

“Ja,” was all he could manage to say.

“Do you want me to? I can if you’re really that needy.”

“No, no,” he muttered. “Why would I do that when being fucked sounds so damn enticing?”

Jester grinned. “Good boy, Caleb. Let me get the gloves.” She went over to the nightstand and grabbed some latex gloves, bringing the strap on and dildo with her, swiping the bottle of lube from the chair. She put on one glove, setting the other aside just in case, then moved her hands to his hips. “Can I flip you over, Caleb? No trying to get off yet, okay?”

As much as he wanted to hump the mattress like his life depended on it, he knew that wasn’t the point. “Ja, Jester, I’m ready.”

“Good!” she said, before flipping him to his stomach like he was a bag of flour. In between her strength and the contact of his dick on the mattress, he moaned surprisingly loud.

“Oh! Look at you, so horny that just touching the mattress makes you moan. What a slut.” She smacked his ass lightly as she inspected his ass. He’d cleaned it meticulously earlier. That might’ve been at least part of the reason why he didn’t want to be the top tonight; didn’t want to waste that effort, now did he? “Permission to eat your ass?” she said. “You look way too tempting.”

As much as Caleb wanted to be proper, all he had the brainpower for was, “Please.”

She said something about how desperate he was and pulled him to the edge of the bed so she could get on her knees behind him. “This good?” she asked.

“Green,” he said, moaning softly from the slide against the sheets.

“Good boy,” she said before diving in eagerly.

Her forked tongue was glorious heaven.

“Oh, fuck!” he cried, turning his face so she could hear him properly, so she could hear every moan she drew out of him. For all the times Jester bragged about his tongue and oh, the wonders it could do when he was between her legs, she truly had a talent for eating him out. Gods, it was wonderful, and he was already a moaning, quaking mess within seconds. It didn’t take long for him to sputter, “Jester, Jester, I’m so close, please make me cum, please, I just need to cum so badly!”

“Cum for me, my love,” she said, the Infernal at the end making him shiver before she returned to her task. Jester no longer held back, eating his ass like it was her last meal and she was already starving. It took seconds for him to come undone. Whatever inhibitions that had kept him quiet were gone now, because he must’ve been screaming as he came. He could feel the warm seed beneath his stomach, and while he knew it would dry and feel gross if they didn’t tend to it while it was wet, Caleb also knew they were changing the sheets and taking a long bath afterwards, anyways. Not the end of the world.

“That would be one,” she said, smiling. “Can you make it to two, Caleb?”

“Ja,” he said, already so fucked out and tired. “Just might need a little bit.”

“Alright,” she said, nodding. “Need a break break, or do you wanna continue and just get hard as we go?”

“Continue, but if it’s too much, I’ll say something.”

“Good boy,” she said, kissing his thigh before getting up and grabbing the lube bottle.

After she put on another glove real quick, she teased his asshole. He was already pretty relaxed, pretty open, but the dick she was going to use was a pretty wide one, and he knew she would rather be safe than sorry. Once she was certain he would let her in, she lubed her other hand up with lightning speed before slowly sliding it in. “That good?” she asked.

“Ja,” he said softly, weakly, with a soft moan.

“Good,” she said. With a steady rhythm, she began to fuck his ass with one finger. “That’s it. Relax for me, Caleb. You’re doing so well.”

“Jester, it feels wonderful,” Caleb muttered, eyes fluttering shut.

“I’m glad.” She leaned down and kissed along his spine as she slowly sped up, drawing more sounds out of him.

After some steady work and a quick confirmation, she slipped in another finger. Then a third. Once he was fully open and satisfied, she tossed aside the gloves and put the strap and dildo on. “Ready, my dear?”

At this point, Caleb’s erection had returned with a vengeance. “Ready as I’ll ever be,” he replied.

“Good,” she said with a grin he could hear before slowly pushed it. The cock had all these wonderful bumps and grooves that felt utterly divine sliding in, though he knew they felt even better once she was fucking him properly. He moaned with both the stimulation and the need.

“Jester,” he said, whining as she moved so, so slowly.

“I know, my dear,” she said, holding his hips with a wonderfully strong grip. “Once I pick up speed, you’ll be in heaven, I know it.”

She was right, he knew. But it didn’t make him any more patient.

Surely enough, however, she quickened her pace, building up to the proper fucking he was craving. Skin hit skin, and once more he was moaning and blissful. “Jester,” he moaned, “Jester,” saying her name like she was his goddess, though that frankly wasn’t far from the truth.

“My love,” she said, “my darling, my husband.” The last one was new. The dick was so damn good he had forgotten that she had proposed, and that their pretty rings were still on the nightstand.

“Please, my dear,” he moaned, once again getting louder, louder. “Please, I’m so close.”

“You want me to fuck you into the mattress, my dear husband?” she asked.

“Bitte,” was all he could manage.

And damn, did she deliver.

Her thrusts were deep, hard, rough, almost painful but too amazing to really hurt. Gods, she was wonderful. Jester’s fingers pressed into his hips so hard they’d probably bruise, but right now he just wanted to cum, wanted her to make him come apart with that cock of hers.

“Jester, I’m close, I’m--”

“Cum,” she ordered.

Like she had pressed a button, another spurt of cum came up from his cock as he cried out. She thrust in once or twice to finish the job, then slowly pulled out. “Your ass is gaping,” she said, proud.

“I’m sure it is,” he said, exhausted. He heard the strap fall to the floor once she’d loosened it off, then she flipped him over to undo the rope.

“You were wonderful, Caleb, absolutely perfect. You did so good.” As she unwrapped him, she quickly cast Cure Wounds over the sore spots, even though he wasn’t really that hurt. She tossed aside the rope and smiled as she leaned over him. “I knew I could get you to cum untouched twice.”

As he blinked away the post-sex fog, Caleb muttered, “Does it count if I was pressed against the mattress the whole time?”

She shrugged. “It’s close enough.” With a smile, Jester massaged his sore muscles and said, “I’ll draw up the bath for you. Light the candle you bought. Alright?”

“Alright,” he said, tired. “Love you,” Caleb added.

“Love you, too,” Jester replied with a smile before moving over to the bathroom so she could tend to him properly.


End file.
